Formal total synthesis of aspergillide A

Yuko Izuchi, Nobuhiro Kanomata, Hiroyuki Koshino, Yayoi Hongo, Tadashi Nakata, Shunya Takahashi

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21 Citations (Scopus)

Abstract

The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4-C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.

Original languageEnglish
Pages (from-to)246-251
Number of pages6
JournalTetrahedron Asymmetry
Volume22
Issue number2
DOIs
Publication statusPublished - 2011 Jan 31

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Izuchi, Y., Kanomata, N., Koshino, H., Hongo, Y., Nakata, T., & Takahashi, S. (2011). Formal total synthesis of aspergillide A. Tetrahedron Asymmetry, 22(2), 246-251. https://doi.org/10.1016/j.tetasy.2011.01.016